I've dealt with this feeling before. And back then, I came away defeated. This was before I discovered YLF. So I tried very hard to 'dress the part' --- and not only was it out of my comfort zone, I gave people the wrong idea about me and then had to use my words to make them understand that I don't really share the same aesthetic (was important in my job) or some of the same sociopolitical attitudes. So I'm declaring a bias before I answer...
However, what I have realized, watching the other ladies here on YLF, is that it IS possible to avoid toeing the line without stepping too far out of line either. (Amy's a super example! So are Rae as she dressed for her earlier job and Shannon in a workplace where her aesthetic stands out, Claire in a social space where many people are less dressy than she is...)
I like Donna's suggestion to switch a few elements around between pictures and see how that goes. Footwear in particular, in the the last two, adds to the conservative styling up top. Now, I get that nudes are leg-lengthening, but the sort of bronze you are wearing in #1 would have much the same effect while feeling a lot less 'conventional classic', I think? Remove flower pin, add different jewellery in #3 --- and make sure your bag and shoes are doing some talking for you. What happens if you add both blazer and leggings, and maybe boots with it? What if add a dramatic scarf to #4, and again, switch out the shoes? Or, wear just the dress and the flower pin, plus carrying a bright bag and wearing bright shoes? Or wear the dress, leggings and the nude pumps --- but add flower pin instead of necklace, no blazer, or just a coloured cardi...? Or take #1, switch to nude pumps and add a bright or patterned belt...?